DiMillo's Marina

DiMillo's Marina has been a fixture of Portland's waterfront since 1979, when Luke DiMillo's grandfather purchased the Long Wharf property and began building the marina around it. Today it is the only marina in the heart of downtown Portland, a location that is grandfathered in, since new marinas are no longer permitted in the city's waterfront central zone.

That location puts DiMillo's at the meeting point of Portland's working waterfront and its tourism economy. The marina serves a steady flow of transient boaters cruising the Maine coast, plus a community of seasonal, winter, and year-round tenants. It also runs a ship store, gift shop, and fuel dock.

Three generations in, the family business now runs on a single system. Luke, who manages the marina today, uses Dockwa for everything from the morning dock walk to the end-of-season renewals.

DiMillo's started with Dockwa for one reason: online transient booking. What began as a single module grew, season by season, into the system the whole marina runs on.

It started with transient

Dockwa gave boaters a way to book online and gave staff one shared source of truth. With the Dockwa app on every phone, iPad, and desktop, everyone on the team sees the same up-to-date information. Each morning, the team sends a pre-arrival message to every boat due in that day, with arrival procedures, slip assignments, contact details, and gate codes.

Then contracts changed everything

After testing Dockwa Contracts with winter tenants for one season, DiMillo's immediately moved its seasonal and year-round tenants over too. Contracts, payments, and insurance collection now live in one workflow, and renewals carry forward instead of starting from scratch. DiMillo's is now in its third full season on Dockwa Contracts.

"I've saved the most time with contracts. Like, it's not even close. It was hundreds of hours putting together contracts and assembling them and sending them out." — Luke DiMillo

• Dock Walk: A guided flow means every dockhand walks the same route and checks the same things. The team gets a live tally of who's in the marina and what's open for the next day.
• Point of Sale: The ship store, gift shop, and fuel dock all run on Dockwa POS. Staff use an iPad and card reader at the fuel house, so they can move around and serve customers. Inventory tracking and reporting sit in the same system as dockage.
• Analytics: Luke compares performance with previous years and checks future bookings, then decides when to use discounts or Dockwa Deals to fill gaps.
• Spotter: Staff can ask plain questions, such as how many reservations are booked, and get answers in seconds. Data that used to be hard to pull is now instant.

"As soon as Dockwa launched their point of sale, it was everything for us. We used it for all of our services." — Luke DiMillo

The biggest change at DiMillo's isn't any single feature. It's that the marina no longer runs on disconnected tools and the people bridging them.

Contracts show the clearest return. Luke went from chasing 30 to 40 tenants each season to one or two. The 105 contracts he once built and sent by hand now renew largely on their own, giving him back hundreds of hours.

Day-to-day operations are steadier, too. Dockhands follow the same dock walk, the front office and fuel dock work from the same live data, and arriving boaters get the information they need before they tie up. When Luke needs to plan ahead, analytics and Spotter answer questions that used to require digging.

"Having everything in one system has changed my life at the marina. It's made everything infinitely easier. It saves a ton of time not having to bounce between systems." — Luke DiMillo, Marina Manager

For a family marina on Portland's working waterfront, that is what an operating system for the marina looks like: fewer things falling through the cracks, and more time for the work that matters on the water.